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ABSTRACT:Wholly aromatic polyketones 7 containing bisbinaphthyl macrocycles were synthesized via P 2 O 5 -MsOH mediated direct condensation reaction of compound 3 with chlorobenzoic acids 4, nucleophilic aromatic substitution reaction of the resulting binaphthyl (5)

Optically active cyclic bis(binaphthyl)s (4a -d), which are composed of aromatics, ethers, and ketonic carbonyls, were synthesized through a two-step nucleophilic aromatic substitution reaction. Bis(binaphthyl) cyclic compounds (4a and 4b) were obtained in moderate yields when difluoride 3a and 3b were employed. On the other hand, bis(binaphthyl)s 4c and 4d were scarcely obtained when 3c and 3d were employed.

Optically active aromatic ether ketone macrocycles containing 2,2 0 -dimethoxy-1,1 0 -binaphthyl-6,6 0 -diyl moieties were synthesized through electrophilic aromatic substitution reaction and stepwise nucleophilic aromatic substitution reactions. Structures of the resulting macrocycles were confirmed by NMR and matrix assisted laser desorption=ionization time of flight (MALDI-TOF) mass measurements.